DE69900441T2 - Oxidative dyeing process and composition for oxidative dyeing of keratin fibers containing a cationic amphiphilic polymer - Google Patents
Oxidative dyeing process and composition for oxidative dyeing of keratin fibers containing a cationic amphiphilic polymerInfo
- Publication number
- DE69900441T2 DE69900441T2 DE69900441T DE69900441T DE69900441T2 DE 69900441 T2 DE69900441 T2 DE 69900441T2 DE 69900441 T DE69900441 T DE 69900441T DE 69900441 T DE69900441 T DE 69900441T DE 69900441 T2 DE69900441 T2 DE 69900441T2
- Authority
- DE
- Germany
- Prior art keywords
- composition
- composition according
- alkyl
- group
- mixtures
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 99
- 238000004043 dyeing Methods 0.000 title claims description 30
- 230000001590 oxidative effect Effects 0.000 title claims description 24
- 102000011782 Keratins Human genes 0.000 title claims description 21
- 108010076876 Keratins Proteins 0.000 title claims description 21
- 229920000642 polymer Polymers 0.000 title claims description 18
- 239000000835 fiber Substances 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 6
- 125000002091 cationic group Chemical group 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 44
- 230000003647 oxidation Effects 0.000 claims description 27
- 238000007254 oxidation reaction Methods 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- 239000002243 precursor Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000007800 oxidant agent Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229920006317 cationic polymer Polymers 0.000 claims description 13
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 11
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 9
- -1 poly(quaternary ammonium) Polymers 0.000 claims description 9
- 229920002678 cellulose Polymers 0.000 claims description 8
- 235000010980 cellulose Nutrition 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 6
- 150000004989 p-phenylenediamines Chemical class 0.000 claims description 5
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims description 4
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 239000000982 direct dye Substances 0.000 claims description 3
- 150000004988 m-phenylenediamines Chemical class 0.000 claims description 3
- 230000000873 masking effect Effects 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000002280 amphoteric surfactant Substances 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Chemical class [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 150000003893 lactate salts Chemical class 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 150000004987 o-phenylenediamines Chemical class 0.000 claims description 2
- 239000003605 opacifier Substances 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 150000003892 tartrate salts Chemical class 0.000 claims description 2
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims description 2
- 230000003750 conditioning effect Effects 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 10
- 239000003086 colorant Substances 0.000 description 8
- 239000002609 medium Substances 0.000 description 6
- 238000004040 coloring Methods 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VIXBPSTZNCRCJE-UHFFFAOYSA-N 1,3-bis[4-amino-n-(2-hydroxyethyl)anilino]propan-2-ol Chemical compound C1=CC(N)=CC=C1N(CCO)CC(O)CN(CCO)C1=CC=C(N)C=C1 VIXBPSTZNCRCJE-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- GZVVXXLYQIFVCA-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=CC=C1N GZVVXXLYQIFVCA-UHFFFAOYSA-N 0.000 description 2
- KEEQZNSCYCPKOJ-UHFFFAOYSA-N 2,6-diethylbenzene-1,4-diamine Chemical compound CCC1=CC(N)=CC(CC)=C1N KEEQZNSCYCPKOJ-UHFFFAOYSA-N 0.000 description 2
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 description 2
- KULOFVMDAJSPOK-UHFFFAOYSA-N 2-(2,5-diaminophenoxy)ethanol Chemical compound NC1=CC=C(N)C(OCCO)=C1 KULOFVMDAJSPOK-UHFFFAOYSA-N 0.000 description 2
- KWSVXCAQFTWTEF-UHFFFAOYSA-N 2-(2,5-diaminophenyl)ethanol Chemical compound NC1=CC=C(N)C(CCO)=C1 KWSVXCAQFTWTEF-UHFFFAOYSA-N 0.000 description 2
- ISCYHXYLVTWDJT-UHFFFAOYSA-N 2-[4-amino-n-(2-hydroxyethyl)anilino]ethanol Chemical compound NC1=CC=C(N(CCO)CCO)C=C1 ISCYHXYLVTWDJT-UHFFFAOYSA-N 0.000 description 2
- BCQDCROHHKDXAT-UHFFFAOYSA-N 2-[4-amino-n-[4-[4-amino-n-(2-hydroxyethyl)anilino]butyl]anilino]ethanol Chemical compound C1=CC(N)=CC=C1N(CCO)CCCCN(CCO)C1=CC=C(N)C=C1 BCQDCROHHKDXAT-UHFFFAOYSA-N 0.000 description 2
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- WNYJRJRHKRZXEO-UHFFFAOYSA-N 2-propan-2-ylbenzene-1,4-diamine Chemical compound CC(C)C1=CC(N)=CC=C1N WNYJRJRHKRZXEO-UHFFFAOYSA-N 0.000 description 2
- 229940018563 3-aminophenol Drugs 0.000 description 2
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- IGMNYECMUMZDDF-UHFFFAOYSA-N homogentisic acid Chemical compound OC(=O)CC1=CC(O)=CC=C1O IGMNYECMUMZDDF-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- NKNCGBHPGCHYCQ-UHFFFAOYSA-N (2,5-diaminophenyl)methanol Chemical compound NC1=CC=C(N)C(CO)=C1 NKNCGBHPGCHYCQ-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- XYAQUYKPDDPZHG-UHFFFAOYSA-N 1-(4-aminoanilino)propan-2-ol Chemical compound CC(O)CNC1=CC=C(N)C=C1 XYAQUYKPDDPZHG-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- WSMJTXVQAZYLAV-UHFFFAOYSA-N 1-methylindol-4-ol Chemical compound C1=CC=C2N(C)C=CC2=C1O WSMJTXVQAZYLAV-UHFFFAOYSA-N 0.000 description 1
- KQGOJGSMIRVVJL-UHFFFAOYSA-N 1-n-methyl-4-n-[4-[4-(methylamino)anilino]butyl]benzene-1,4-diamine Chemical compound C1=CC(NC)=CC=C1NCCCCNC1=CC=C(NC)C=C1 KQGOJGSMIRVVJL-UHFFFAOYSA-N 0.000 description 1
- XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 description 1
- LHGQFZQWSOXLEW-UHFFFAOYSA-N 1h-pyrazole-4,5-diamine Chemical compound NC=1C=NNC=1N LHGQFZQWSOXLEW-UHFFFAOYSA-N 0.000 description 1
- JWLQULBRUJIEHY-UHFFFAOYSA-N 2,3-dihydro-1h-indol-6-ol Chemical compound OC1=CC=C2CCNC2=C1 JWLQULBRUJIEHY-UHFFFAOYSA-N 0.000 description 1
- SYEYEGBZVSWYPK-UHFFFAOYSA-N 2,5,6-triamino-4-hydroxypyrimidine Chemical compound NC1=NC(N)=C(N)C(O)=N1 SYEYEGBZVSWYPK-UHFFFAOYSA-N 0.000 description 1
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 description 1
- WCPGNFONICRLCL-UHFFFAOYSA-N 2-(2,4-diaminophenoxy)ethanol Chemical compound NC1=CC=C(OCCO)C(N)=C1 WCPGNFONICRLCL-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- SBUMIGFDXJIPLE-UHFFFAOYSA-N 2-(3-amino-4-methoxyanilino)ethanol Chemical compound COC1=CC=C(NCCO)C=C1N SBUMIGFDXJIPLE-UHFFFAOYSA-N 0.000 description 1
- WFXLRLQSHRNHCE-UHFFFAOYSA-N 2-(4-amino-n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C=C1 WFXLRLQSHRNHCE-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- DEZOGYCXWGTILF-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]pyrazole-3,4-diamine Chemical compound NC1=C(N)C=NN1CC1=CC=C(Cl)C=C1 DEZOGYCXWGTILF-UHFFFAOYSA-N 0.000 description 1
- BGRBURMLBAACID-UHFFFAOYSA-N 2-[4-amino-3-chloro-n-(2-hydroxyethyl)anilino]ethanol Chemical compound NC1=CC=C(N(CCO)CCO)C=C1Cl BGRBURMLBAACID-UHFFFAOYSA-N 0.000 description 1
- KBHHZOYDILVUBF-UHFFFAOYSA-N 2-[4-amino-n-(2-hydroxyethyl)-3-methylanilino]ethanol Chemical compound CC1=CC(N(CCO)CCO)=CC=C1N KBHHZOYDILVUBF-UHFFFAOYSA-N 0.000 description 1
- FLCAOAGLACNSPB-UHFFFAOYSA-N 2-[4-amino-n-[2-[4-amino-n-(2-hydroxyethyl)anilino]ethyl]anilino]ethanol Chemical compound C1=CC(N)=CC=C1N(CCO)CCN(CCO)C1=CC=C(N)C=C1 FLCAOAGLACNSPB-UHFFFAOYSA-N 0.000 description 1
- HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 description 1
- ALQKEYVDQYGZDN-UHFFFAOYSA-N 2-amino-6-methylphenol Chemical compound CC1=CC=CC(N)=C1O ALQKEYVDQYGZDN-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- FXFTWEVIIHVHDS-UHFFFAOYSA-N 2-fluorobenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(F)=C1 FXFTWEVIIHVHDS-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- XOAXOKSJNVLLHZ-UHFFFAOYSA-N 2-methylpyrazole-3,4-diamine Chemical compound CN1N=CC(N)=C1N XOAXOKSJNVLLHZ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- MWKPYVXITDAZLL-UHFFFAOYSA-N 4-[3-(2,4-diaminophenoxy)propoxy]benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1OCCCOC1=CC=C(N)C=C1N MWKPYVXITDAZLL-UHFFFAOYSA-N 0.000 description 1
- PZKNKZNLQYKXFV-UHFFFAOYSA-N 4-amino-2-(aminomethyl)phenol Chemical compound NCC1=CC(N)=CC=C1O PZKNKZNLQYKXFV-UHFFFAOYSA-N 0.000 description 1
- WSEFOZIMAJPJHW-UHFFFAOYSA-N 4-amino-2-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C(CO)=C1 WSEFOZIMAJPJHW-UHFFFAOYSA-N 0.000 description 1
- RGKJLNMYCNSVKZ-UHFFFAOYSA-N 4-amino-2-(methoxymethyl)phenol Chemical compound COCC1=CC(N)=CC=C1O RGKJLNMYCNSVKZ-UHFFFAOYSA-N 0.000 description 1
- UPHYVIFVOBTQNW-UHFFFAOYSA-N 4-amino-2-[(2-hydroxyethylamino)methyl]phenol Chemical compound NC1=CC=C(O)C(CNCCO)=C1 UPHYVIFVOBTQNW-UHFFFAOYSA-N 0.000 description 1
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 description 1
- DHKIYDNMIXSKQP-UHFFFAOYSA-N 4-amino-3-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C=C1CO DHKIYDNMIXSKQP-UHFFFAOYSA-N 0.000 description 1
- MNPLTKHJEAFOCA-UHFFFAOYSA-N 4-amino-3-fluorophenol Chemical compound NC1=CC=C(O)C=C1F MNPLTKHJEAFOCA-UHFFFAOYSA-N 0.000 description 1
- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 description 1
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 description 1
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical compound OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 description 1
- POKISONDDBRXBK-UHFFFAOYSA-N 4-n,4-n,2-trimethylbenzene-1,4-diamine Chemical compound CN(C)C1=CC=C(N)C(C)=C1 POKISONDDBRXBK-UHFFFAOYSA-N 0.000 description 1
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 description 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- UOWYGPTYSRURDP-UHFFFAOYSA-N 4-n,4-n-dipropylbenzene-1,4-diamine Chemical compound CCCN(CCC)C1=CC=C(N)C=C1 UOWYGPTYSRURDP-UHFFFAOYSA-N 0.000 description 1
- QZHXKQKKEBXYRG-UHFFFAOYSA-N 4-n-(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1 QZHXKQKKEBXYRG-UHFFFAOYSA-N 0.000 description 1
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- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 1
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- SBJKKFFYIZUCET-UHFFFAOYSA-N Dehydroascorbic acid Natural products OCC(O)C1OC(=O)C(=O)C1=O SBJKKFFYIZUCET-UHFFFAOYSA-N 0.000 description 1
- KZQYIMCESJLPQH-UHFFFAOYSA-N Demethylated antipyrine Chemical compound N1C(C)=CC(=O)N1C1=CC=CC=C1 KZQYIMCESJLPQH-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
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- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 235000020960 dehydroascorbic acid Nutrition 0.000 description 1
- 239000011615 dehydroascorbic acid Substances 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- BKEFUBHXUTWQED-UHFFFAOYSA-N n-(4-amino-3-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C(O)=C1 BKEFUBHXUTWQED-UHFFFAOYSA-N 0.000 description 1
- 150000004950 naphthalene Polymers 0.000 description 1
- 150000002790 naphthalenes Polymers 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 101150018444 sub2 gene Proteins 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/415—Aminophenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/731—Cellulose; Quaternized cellulose derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Toxicology (AREA)
- Dermatology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Textile Engineering (AREA)
- Cosmetics (AREA)
Description
Die vorliegende Erfindung betrifft ein Verfahren zum oxidativen Färben von Keratinfasern und insbesondere menschlichen Keratinfasern, wie dem Haar, unter Verwendung von Zusammensetzungen, die in einem zum Färben geeigneten Medium mindestens ein Farbstoffvorprodukt eines Oxidationsfarbstoffes, gegebenenfalls einen oder mehrere Kuppler, mindestens ein Oxidationsmittel sowie mindestens ein amphiphiles kationisches Polymer enthalten.The present invention relates to a process for the oxidative dyeing of keratin fibers and in particular human keratin fibers, such as hair, using compositions which contain, in a medium suitable for dyeing, at least one dye precursor of an oxidation dye, optionally one or more couplers, at least one oxidizing agent and at least one amphiphilic cationic polymer.
Es ist bekannt, Keratinfasern und insbesondere das Haar mit Farbmittelzusammensetzungen zu färben, die Farbstoffvorprodukte von Oxidationsfarbstoffen enthalten, die im allgemeinen als Oxidationsbasen bezeichnet werden, insbesondere o- oder p-Phenylendiamine, o- oder p- Aminophenole und heterocyclische Basen.It is known to dye keratin fibers, and in particular hair, with dye compositions containing dye precursors of oxidation dyes, generally referred to as oxidation bases, in particular o- or p-phenylenediamines, o- or p-aminophenols and heterocyclic bases.
Die Farbstoffvorprodukte von Oxidationsfarbstoffen sind ursprünglich farblose oder schwach gefärbte Verbindungen, die das Haar in Gegenwart eines Oxidationsmittels zu färben vermögen. Die Bildung von farbigen Verbindungen ergibt sich entweder durch die Kondensation der "Oxidationsbasen" untereinander oder durch die Kondensation von "Oxidationsbasen" mit Farbnuancierungsmitteln oder "Kupplern"; diese liegen im allgemeinen in Farbmittelzusammensetzungen vor, die zum oxidativen Färben verwendet werden, wobei es sich insbesondere um m- Phenylendiamine, m-Aminophenole, m-Dihydroxybenzole und verschiedene heterocyclische Verbindungen handelt.The dye precursors of oxidation dyes are originally colourless or slightly coloured compounds which are able to colour the hair in the presence of an oxidising agent. The formation of coloured compounds results either from the condensation of the "oxidation bases" with one another or from the condensation of "oxidation bases" with colour shading agents or "couplers"; these are generally present in colouring compositions used for oxidative colouring, in particular m-phenylenediamines, m-aminophenols, m-dihydroxybenzenes and various heterocyclic compounds.
Durch die Mannigfaltigkeit der beteiligten Moleküle, wobei es sich einerseits um die "Oxidationsbasen" und andererseits um die "Kuppler" handelt, kann eine große Farbpalette hergestellt werden.Due to the variety of molecules involved, which are on the one hand the "oxidation bases" and on the other hand the "couplers", a large range of colors can be produced.
Beim Aufbringen auf das Haar muß das Produkt zum Färben dort verbleiben, wo es aufgetragen wurde, und sollte nicht über das Gesicht laufen oder über die Bereiche hinauslaufen, die gefärbt werden sollen. Es wurden bis heute für diesen Zweck herkömmliche Verdickungsmittel eingesetzt, beispielsweise vernetzte Polyacrylsäure, Hydroxyethylcellulosen, Wachse oder verschiedene nichtionische grenzflächenaktive Stoffe, die bei geeigneter Auswahl als Verdickungsmittel oder sogar Gelbildner für wäßrige Medien wirken.When applied to the hair, the colouring product must remain where it was applied and should not run down the face or over the areas to be coloured. To date, conventional thickeners have been used for this purpose, such as cross-linked polyacrylic acid, hydroxyethyl celluloses, waxes or various non-ionic surfactants, which, when properly selected, act as thickeners or even gelling agents for aqueous media.
Die Anmelderin hat jedoch festgestellt, daß die Bestandteile vom Typ der herkömmlichen Verdickungsmittel, grenzflächenaktiven Stoffe und Lösungsmittel im allgemeinen das Aufziehen des Farbmittels auf die Fasern behindern, was durch weniger leuchtende Farbnuancen zum Ausdruck kommt. Für eine gleichwertige Farbsättigung ist es daher erforderlich, höhere Farbstoffmengen und mehr Lösungsmittel und/oder größere Mengen an grenzflächenaktiven Stoffen zu verwenden, um diese zu lösen.However, the applicant has found that components of the type of conventional thickeners, surfactants and solvents generally hinder the absorption of the dye onto the fibres, resulting in less bright shades of colour. To achieve equivalent colour saturation, it is therefore necessary to use larger quantities of dye and more solvent and/or larger quantities of surfactants to dissolve them.
Die Anmelderin hat außerdem festgestellt, daß die Zusammensetzungen, die das (die) Farbstoffvorprodukt(e) von Oxidationsfarbstoffen und gegebenenfalls den (die) Kuppler enthalten und mit herkömmlichen Verdikkungsmitteln eingedickt sind, einen Teil ihrer Geleigenschaft verlieren, wenn sie mit der Zusammensetzung vermischt werden, die das Oxidationsmittel enthält.The applicant has also found that compositions containing the dye precursor(s) of oxidation dyes and optionally the coupler(s) and thickened with conventional thickeners lose part of their gelling properties when mixed with the composition containing the oxidizing agent.
Nach umfangreichen, auf diesem Gebiet durchgeführten Untersuchungen hat die Anmelderin festgestellt, daß Zusammensetzungen zum oxidativen Färben hergestellt werden können, die auch nach dem Mischen mit dem Oxidationsmittel nicht fließen und daher besser dort verbleiben, wo sie aufgetragen wurden, wenn eine wirksame Menge eines speziellen, assoziativen kationischen Polymers als VerdickungsmittelAfter extensive research in this field, the Applicant has found that compositions for oxidative dyeing can be prepared which do not flow even after mixing with the oxidizing agent and therefore remain better where they have been applied, if an effective amount of a specific associative cationic polymer is used as a thickener.
(i) entweder in die Zusammensetzung, die das Farbstoffvorprodukt eines Oxidationsfarbstoffes oder die Farbstoffvorprodukte von Oxidationsfarbstoffen und gegebenenfalls den Kuppler oder die Kuppler enthält (Zusammensetzung A),(i) either in the composition containing the dye precursor of an oxidation dye or the dye precursors of oxidation dyes and, where appropriate, the coupler or couplers (composition A),
(ii) oder die oxidierende Zusammensetzung (Zusammensetzung B),(ii) or the oxidizing composition (composition B),
(iii) oder gleichzeitig in beide Zusammensetzungen (A + B) eingearbeitet wird. Diese Zusammensetzungen führen im übrigen im Vergleich mit äquivalenten Zusammensetzungen, die herkömmliche Verdickungssysteme enthalten, zu satteren (leuchtenderen) und kräftigeren Farbschattierungen.(iii) or simultaneously incorporated into both compositions (A + B). These compositions also result in richer (brighter) and more intense shades of colour compared to equivalent compositions containing conventional thickening systems.
Die erhaltenen Färbungen sind im übrigen gegenüber Schweiß sehr beständig.The resulting colours are also very resistant to sweat.
Im Sinne der vorliegenden Erfindung ist die Buntheit (Leuchtkraft) in dem colorimetrischen System L*, a*, b* der Internationalen Beleuchtungskommission (Commision Internationale de 1'Éclairage CIE) durch den Wert C* definiert. Dieser Wert ist die Quadratwurzel der Summe a² + b² (+a ist rot, -a ist grün, +b ist gelb, -b ist blau). Die Farbnuance ist um so leuchtender, je höherer der Wert C* ist. In diesem System definiert L* die Helligkeit. Die Farbnuance ist um so kräftiger, je niedriger der Wert L* ist (0 = schwarz, 100 = weiß).For the purposes of the present invention, the chroma (luminosity) is defined in the colorimetric system L*, a*, b* of the International Commission on Illumination (Commision Internationale de 1'Éclairage CIE) by the value C*. This value is the square root of the sum a² + b² (+a is red, -a is green, +b is yellow, -b is blue). The higher the value C*, the brighter the color nuance. In this system, L* defines the brightness. The lower the value L*, the stronger the color nuance (0 = black, 100 = white).
Durch die vorliegende Erfindung ist es außerdem möglich, die Verwendung von grenzflächenaktiven Stoffen in vorteilhafter Weise einzuschränken oder zu vermeiden.The present invention also makes it possible to advantageously limit or avoid the use of surfactants.
Durch die vorliegende Erfindung kann im Vergleich mit herkömmlichen, im Stand der Technik bekannten Verfahren auch die Menge der in der Zusammensetzung zum Färben verwendeten Farbmittel vermindert werden.The present invention also makes it possible to reduce the amount of colorants used in the coloring composition compared to conventional methods known in the art.
Gemäß der vorliegenden Erfindung werden unter "assoziativen Polymeren" wasserlösliche Polymere verstanden, die befähigt sind, sich in einem wäßrigen Medium reversibel untereinander oder mit anderen Molekülen zu verbinden. Die chemische Struktur dieser Polymere, die im allgemeinen als "amphiphile Polymere" bezeichnet werden, ist durch die Gegenwart von hydrophilen Bereichen, die die Wasserlöslichkeit gewährleisten, und hydrophoben Bereichen gekennzeichnet, über die sich die Polymere in einem wäßrigen Medium miteinander oder mit den hydrophoben Bereichen anderer Moleküle anordnen.According to the present invention, "associative polymers" are understood to mean water-soluble polymers capable of reversibly combining with one another or with other molecules in an aqueous medium. The chemical structure of these polymers, generally referred to as "amphiphilic polymers", is characterized by the presence of hydrophilic regions which ensure water solubility and hydrophobic regions by means of which the polymers associate with one another or with the hydrophobic regions of other molecules in an aqueous medium.
Die vorliegende Erfindung betrifft daher ein Verfahren zum Färben von Keratinfasern und insbesondere menschlichen Keratinfasern, wie Haaren, das darin besteht, auf die Fasern eine Zusammensetzung zum oxidativen Färben (A) aufzutragen, die in einem zum Färben geeigneten Medium mindestens ein Farbstoffvorprodukt eines Oxidationsfarbstoffes und gegebenenfalls einen oder mehrer Kuppler enthält, und die Farbe in einem alkalischen, neutralen oder sauren Medium mit einer oxidierenden Zusammensetzung (B) zu entwickeln, die ein Oxidationsmittel enthält, wobei mindestens eine der Zusammensetzungen (A) und (B) ferner in einer wirksamen Menge mindestens ein amphiphiles kationisches Polymer enthält, das unterThe present invention therefore relates to a process for dyeing keratin fibers and in particular human keratin fibers, such as hair, which consists in applying to the fibers an oxidative dyeing composition (A) containing, in a medium suitable for dyeing, at least one dye precursor of an oxidation dye and optionally one or more couplers, and in developing the color in an alkaline, neutral or acidic medium with an oxidizing composition (B) containing an oxidizing agent, at least one of the compositions (A) and (B) further containing, in an effective amount, at least one amphiphilic cationic polymer which, among
- quaternisierten Cellulosen, die mit Gruppen mit mindestens einer Fettkette, die unter den Gruppen Alkyl, Arylalkyl oder Alkylaryl mit mindestens 8 Kohlenstoffatomen ausgewählt sind, oder deren Gemischen modifiziert sind; und- quaternized celluloses modified with groups containing at least one fatty chain selected from the group consisting of alkyl, arylalkyl or alkylaryl containing at least 8 carbon atoms, or mixtures thereof; and
- quaternisierten Hydroxyethylcellulosen, die mit Gruppen mit mindestens einer Fettkette, die unter den Gruppen Alkyl, Arylalkyl oder Alkylaryl mit mindestens 8 Kohlenstoffatomen ausgewählt sind, oder deren Gemischen modifiziert sind;- quaternized hydroxyethylcelluloses modified with groups containing at least one fatty chain selected from the group consisting of alkyl, arylalkyl or alkylaryl containing at least 8 carbon atoms, or mixtures thereof;
ausgewählt ist, wobei die Zusammensetzungen (A) und (B) unmittelbar vor der Anwendung vermischt werden oder nacheinander auf die Keratinfasern aufgebracht werden.is selected, wherein the compositions (A) and (B) are mixed immediately before application or are applied successively to the keratin fibers.
Die Erfindung betrifft auch Zusammensetzungen zum oxidativen Färben von Keratinfasern und insbesondere menschlichen Keratinfasern, die in einem zum Färben geeigneten Medium mindestens ein Farbstoffvorprodukt eines Oxidationsfarbstoffes und gegebenenfalls einen oder mehrere Kuppler und mindestens ein amphiphiles kationisches Polymer enthalten, das ausgewählt ist unter:The invention also relates to compositions for the oxidative dyeing of keratin fibers and in particular human keratin fibers, which contain, in a medium suitable for dyeing, at least one dye precursor of an oxidation dye and optionally one or more couplers and at least one amphiphilic cationic polymer selected from:
- quaternisierten Cellulosen, die mit Gruppen mit mindestens einer Fettkette, die unter den Gruppen Alkyl, Arylalkyl oder Alkylaryl mit mindestens 8 Kohlenstoffatomen ausgewählt sind, oder deren Gemischen modifiziert sind; und- quaternized celluloses modified with groups containing at least one fatty chain selected from the group consisting of alkyl, arylalkyl or alkylaryl containing at least 8 carbon atoms, or mixtures thereof; and
- quaternisierten Hydroxyethylcellulosen, die mit Gruppen mit mindestens einer Fettkette, die unter den Gruppen Alkyl, Arylalkyl oder Alkylaryl mit mindestens 8 Kohlenstoffatomen ausgewählt sind, oder deren Gemischen modifiziert sind.- quaternized hydroxyethylcelluloses modified with groups containing at least one fatty chain selected from the group consisting of alkyl, arylalkyl or alkylaryl containing at least 8 carbon atoms, or mixtures thereof.
Ein dritter Gegenstand der Erfindung ist eine oxidierende Zusammensetzung, die dazu dient, die Farbe einer Zusammensetzung zum oxidativen Färben zu entwickeln und die ein Oxidationsmittel und mindestens ein oben definiertes amphiphiles kationisches Polymer enthält.A third subject of the invention is an oxidizing composition intended to develop the color of an oxidative dyeing composition and which contains an oxidizing agent and at least one amphiphilic cationic polymer as defined above.
Ein weiterer Gegenstand der Erfindung ist eine gebrauchsfertige Zusammensetzung zum Färben von Keratinfasern, die mindestens ein Farbstoffvorprodukt eines Oxidationsfarbstoffes, gegebenenfalls einen oder mehrere Kuppler, mindestens ein oben definiertes amphiphiles kationisches Polymer und mindestens ein Oxidationsmittel enthält.Another subject of the invention is a ready-to-use composition for dyeing keratin fibers, which contains at least one dye precursor of an oxidation dye, optionally one or more couplers, at least one amphiphilic cationic polymer as defined above and at least one oxidizing agent.
Die Erfindung betrifft auch Vorrichtungen zum Färben mit mehreren Abteilungen oder "Kits" zum Färben, die mindestens zwei Abteilungen aufweisen, wobei eine Abteilung eine Zusammensetzung (A), die in einem zum Färben geeigneten Medium mindestens ein Farbstoffvorprodukt eines Oxidationsfarbstoffes und gegebenenfalls einen oder mehrere Kuppler enthält, und eine weitere Abteilung die oxidierende Zusammensetzung (B) enthält, die mindestens ein Oxidationsmittel enthält, wobei mindestens eine der Zusammensetzungen (A) und (B) ferner in einer wirksamen Menge mindestens ein oben definiertes amphiphiles kationisches Polymer enthält.The invention also relates to dyeing devices with several compartments or dyeing kits comprising at least two compartments, one compartment containing a composition (A) comprising, in a medium suitable for dyeing, at least one dye precursor of an oxidation dye and optionally one or more couplers and a further compartment contains the oxidizing composition (B) which contains at least one oxidizing agent, wherein at least one of the compositions (A) and (B) further contains in an effective amount at least one amphiphilic cationic polymer as defined above.
Die Alkylgruppen der oben genannten quaternisierten Cellulosen oder Hydroxyethylcellulosen enthalten vorzugsweise 8 bis 30 Kohlenstoffatome. Die Arylgruppen bedeuten vorzugsweise die Gruppen Phenyl, Benzyl, Naphthyl oder Anthryl.The alkyl groups of the above-mentioned quaternized celluloses or hydroxyethyl celluloses preferably contain 8 to 30 carbon atoms. The aryl groups preferably represent the groups phenyl, benzyl, naphthyl or anthryl.
Als Beispiele für quaternisierte Alkylhydroxyethylcellulosen mit C&sub8;&submin;&sub3;&sub0;- Fettketten können die Produkte QUATRISOFT LM 200, QUATRISOFT LM-X 529-18-A, QUATRISOFT LM-X 529-18-B (C&sub1;&sub2;-Alkyl) und QUATRISOFT LM-X 529-8 (C&sub1;&sub8;-Alkyl) der Firma AMERCHOL und die Produkte CRODACEL QM, CRODACEL QL (C&sub1;&sub2;-Alkyl) und CRODACEL QS (C&sub1;&sub8;-Alkyl) der Firma CRODA angegeben werden.Examples of quaternized alkylhydroxyethylcelluloses with C8-30 fatty chains are the products QUATRISOFT LM 200, QUATRISOFT LM-X 529-18-A, QUATRISOFT LM-X 529-18-B (C12-alkyl) and QUATRISOFT LM-X 529-8 (C18-alkyl) from AMERCHOL and the products CRODACEL QM, CRODACEL QL (C12-alkyl) and CRODACEL QS (C18-alkyl) from CRODA.
Die in den erfindungsgemäßen Zusammensetzungen verwendeten amphiphilen kationischen Polymere liegen vorzugsweise in einem Mengenanteil von 0,05 bis 10 Gew.-% und insbesondere 0,1 bis 5 Gew.-%, bezogen auf das Gesamtgewicht der Zusammensetzung zum oxidativen Färben (A) oder der oxidierenden Zusammensetzung (B), vor.The amphiphilic cationic polymers used in the compositions according to the invention are preferably present in a proportion of 0.05 to 10% by weight and in particular 0.1 to 5% by weight, based on the total weight of the oxidative dyeing composition (A) or the oxidizing composition (B).
Die im Rahmen der vorliegenden Erfindung verwendbaren Oxidationsbasen sind unter den herkömmlich zum oxidativen Färben verwendeten Verbindungen ausgewählt. Es können insbesondere genannt werden:The oxidation bases that can be used in the context of the present invention are selected from the compounds conventionally used for oxidative dyeing. In particular, mention may be made of:
- die p-Phenylendiamine der folgenden Formel (I) und die Additionssalze dieser Verbindungen mit einer Säure: - the p-phenylenediamines of the following formula (I) and the addition salts of these compounds with an acid:
worin bedeuten:where:
R&sub1; Wasserstoff, C&sub1;&submin;&sub4;-Alkyl, C&sub1;&submin;&sub4;-Monohydroxyalkyl, C&sub2;&submin;&sub4;-Polyhydroxyalkyl oder 4'-Aminophenyl;R&sub1; hydrogen, C1-4 alkyl, C1-4 monohydroxyalkyl, C2-4 polyhydroxyalkyl or 4'-aminophenyl;
R&sub2; Wasserstoff, C&sub1;&submin;&sub4;-Alkyl, C&sub1;&submin;&sub4;-Monohydroxyalkyl oder C&sub2;&submin;&sub4;- Polyhydroxyalkyl;R&sub2; hydrogen, C1-4 alkyl, C1-4 monohydroxyalkyl or C2-4 polyhydroxyalkyl;
R&sub3; Wasserstoff, Halogen, wie Chlor, C&sub1;&submin;&sub4;-Alkyl, Sulfo, Carboxy, C&sub1;&submin;&sub4;- Monohydroxyalkyl oder C&sub1;&submin;&sub4;-Hydroxyalkoxy;R&sub3; hydrogen, halogen such as chlorine, C1-4 alkyl, sulfo, carboxy, C1-4 monohydroxyalkyl or C1-4 hydroxyalkoxy;
R&sub4; Wasserstoff oder C&sub1;&submin;&sub4;-Alkyl.R₄ is hydrogen or C₁₋₄-alkyl.
Von den p-Phenylendiaminen der oben genannten Formel (I) können insbesondere genannt werden: p-Phenylendiamin, p-Toluylendiamin, 2- Chlor-p-phenylendiamin, 2,3-Dimethyl-p-phenylendiamin, 2,6-Dimethylp-phenylendiamin, 2,6-Diethyl-p-phenylendiamin, 2, 5-Dimethyl-p- phenylendiamin, N,N-Dimethyl-p-phenylendiamin, N,N-Diethyl-p- phenylendiamin, N,N-Dipropyl-p-phenylendiamin, 4-Amino-N,N-diethyl- 3-methyl-anilin, N,N-Bis(β-hydroxyethyl)-p-phenylendiamin, 4-Amino - N,N-bis(β-hydroxyethyl)-3-methyl-anilin, 4-Amino-3-chlor-N,N-bis(β- hydroxyethyl)-anilin, 2-β-Hydroxyethyl-p-phenylendiamin, 2-Fluor-p- phenylendiamin, 2-Isopropyl-p-phenylendiamin, N-(β-Hydroxypropyl)-p- phenylendiamin, 2-Hydroxymethyl-p-phenylendiamin, N,N-Dimethyl-3- methyl-p-phenylendiamin, N-Ethyl-N-β-hydroxyethyl-p-phenylendiamin, N-(β,γ-Dihydroxypropyl)-p-phenylendiamin, N-(4'-Aminophenyl)-p- phenylendiamin, N-Phenyl-p-phenylendiamin, 2-β-Hydroxyethyloxy-p- phenylendiamin und deren Additionssalze mit einer Säure.Among the p-phenylenediamines of formula (I) above, there may be mentioned in particular: p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, 2,6-dimethylp-phenylenediamine, 2,6-diethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, N,N-dimethyl-p-phenylenediamine, N,N-diethyl-p-phenylenediamine, N,N-dipropyl-p-phenylenediamine, 4-amino-N,N-diethyl-3-methyl-aniline, N,N-bis(β-hydroxyethyl)-p-phenylenediamine, 4-amino-N,N-bis(β-hydroxyethyl)-3-methyl-aniline, 4-Amino-3-chloro-N,N-bis(β-hydroxyethyl)aniline, 2-β-hydroxyethyl-p-phenylenediamine, 2-fluoro-p-phenylenediamine, 2-isopropyl-p-phenylenediamine, N-(β-hydroxypropyl)-p-phenylenediamine, 2-hydroxymethyl-p-phenylenediamine, N,N-dimethyl-3-methyl-p-phenylenediamine, N-ethyl-N-β-hydroxyethyl-p-phenylenediamine, N-(β,γ-dihydroxypropyl)-p-phenylenediamine, N-(4'-aminophenyl)-p-phenylenediamine, N-phenyl-p-phenylenediamine, 2-β-hydroxyethyloxy-p-phenylenediamine and their addition salts with an acid.
Von den p-Phenylendiaminen der Formel (I) werden insbesondere bevorzugt: p-Phenylendiamin, p-Toluylendiamin, 2-Isopropyl-p-phenylendiamin, 2-β-Hydroxyethyl-p-phenylendiamin, 2-β-Hydroxyethyloxy-pphenylendiamin, 2,6-Dimethyl-p-phenylendiamin, 2,6-Diethyl-pphenylendiamin, 2,3-Dimethyl-p-phenylendiamin, N,N-Bis(β-hydroxyethyl)-p-phenylendiamin, 2-Chlor-p-phenylendiamin und deren Additionssalze mit einer Säure.Of the p-phenylenediamines of formula (I), the following are particularly preferred: p-phenylenediamine, p-toluenediamine, 2-isopropyl-p-phenylenediamine, 2-β-hydroxyethyl-p-phenylenediamine, 2-β-hydroxyethyloxy-p-phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2,6-diethyl-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, N,N-bis(β-hydroxyethyl)-p-phenylenediamine, 2-chloro-p-phenylenediamine and their addition salts with an acid.
- die Bisphenylalkylendiamine der folgenden Formel (II) und die Additionssalze dieser Verbindungen mit einer Säure: - the bisphenylalkylenediamines of the following formula (II) and the addition salts of these compounds with an acid:
worin bedeuten:where:
Q&sub1; und Q&sub2;, die identisch oder voneinander verschieden sind, Hydroxy oder NHR&sub8;, wobei R&sub8; Wasserstoff oder C&sub1;&submin;&sub4;-Alkyl bedeutet,Q₁ and Q₂, which are identical or different, are hydroxy or NHR₈, where R₈ is hydrogen or C₁₋₄-alkyl,
R&sub5; Wasserstoff, C&sub1;&submin;&sub4;-Alkyl, C&sub1;&submin;&sub4;-Monohydroxyalkyl, C&sub2;&submin;&sub4;-Polyhydroxyalkyl oder C&sub1;&submin;&sub4;-Aminoalkyl, wobei die Aminoguppe substituiert sein kann,R₅ is hydrogen, C₁₋₄-alkyl, C₁₋₄-monohydroxyalkyl, C₂₋₄-polyhydroxyalkyl or C₁₋₄-aminoalkyl, where the amino group may be substituted,
R&sub6; und R&sub7;, die identisch oder voneinander verschieden sind, ein Wasserstoff- oder Halogenatom oder C&sub1;&submin;&sub4;-Alkyl,R₆ and R₇, which are identical or different, are a hydrogen or halogen atom or C₁₋₄alkyl,
W eine Gruppe, die unter den folgenden Gruppen ausgewählt ist:W a group selected from the following groups:
-(CH&sub2;)n-; -(CH&sub2;)m-O-(CH&sub2;)m-; -(CH&sub2;)m-CHOH-(CH&sub2;)m- und-(CH₂)n-; -(CH₂)m-O-(CH₂)m-; -(CH₂)m-CHOH-(CH₂)m- and
-(CH&sub2;)m-N(CH&sub3;)-(CH&sub2;)m-;-(CH2 )m-N(CH3 )-(CH2 )m-;
wobei n Null oder eine ganze Zahl von 1 bis 8 und m Null oder eine ganze Zahl von 1 bis 4 bedeutet.where n is zero or an integer from 1 to 8 and m is zero or an integer from 1 to 4.
Von den Bisphenylalkylendiaminen der oben genannten Formel (II) können insbesondere genannt werden: N,N'-Bis(β-hydroxyethyl)-N,N'-bis(4- aminophenyl)-1,3-diamino-2-propanol, N,N'-Bis(β-hydroxyethyl)-N,N'- bis(4-aminophenyl)-ethylendiamin, N,N'-Bis(4-aminophenyl)-tetramethylendiamin, N,N'-Bis(β-hydroxyethyl)-N,N'-bis(4-aminophenyl)- tetramethylendiamin, N,N'-Bis(4-methylaminophenyl)-tetramethylendiamin, N,N'-Bis(β-hydroxyethyl)-N,N'-bis(4-aminophenyl)-tetramethylendiamin, N,N'-Bis(ethyl)-N,N'-bis(4-amino-3-methylphenyl)-ethylendiamin und die Additionssalze dieser Verbindungen mit einer Säure.Among the bisphenylalkylenediamines of the above formula (II) there may be mentioned in particular: N,N'-bis(β-hydroxyethyl)-N,N'-bis(4- aminophenyl)-1,3-diamino-2-propanol, N,N'-bis(β-hydroxyethyl)-N,N'-bis(4-aminophenyl)-ethylenediamine, N,N'-bis(4-aminophenyl)-tetramethylenediamine, N,N'-bis(β-hydroxyethyl)-N,N'-bis(4-aminophenyl)-tetramethylenediamine, N,N'-bis(4-methylaminophenyl)-tetramethylenediamine, N,N'-bis(β-hydroxyethyl)-N,N'-bis(4-aminophenyl)-tetramethylenediamine, N,N'-bis(ethyl)-N,N'-bis(4-amino-3-methylphenyl)-ethylenediamine and the addition salts of these compounds with an acid.
Von den Bisphenylalkylendiaminen der Formel (II) werden das N,N'- Bis(β-hydroxyethyl)-N,N'-bis(4'-aminophenyl)-1,3-diamino-2-propanol oder die Additionssalze dieser Verbindung mit einer Säure besonders bevorzugt.Of the bisphenylalkylenediamines of formula (II), N,N'- bis(β-hydroxyethyl)-N,N'-bis(4'-aminophenyl)-1,3-diamino-2-propanol or the addition salts of this compound with an acid are particularly preferred.
- die p-Aminophenole der folgenden Formel (III) und die Additionssalze dieser Verbindungen mit einer Säure: - the p-aminophenols of the following formula (III) and the addition salts of these compounds with an acid:
worin bedeuten:where:
R&sub9; Wasserstoff, C&sub1;&submin;&sub4;-Alkyl, C&sub1;&submin;&sub4;-Monohydroxyalkyl, C&sub1;&submin;&sub4;-Alkoxy-C&sub1;&submin;&sub4;-alkyl, C&sub1;&submin;&sub4;-Aminoalkyl oder C&sub1;&submin;&sub4;-Hydroxyalkyl-C&sub1;&submin;&sub4;-aminnalkyl;R&sub9; Hydrogen, C1-4 alkyl, C1-4 monohydroxyalkyl, C1-4 alkoxy-C1-4 alkyl, C1-4 aminoalkyl or C1-4 alkyl ;4-Hydroxyalkyl-C1-4 amine nalkyl;
Rio Wasserstoff, Fluor, C&sub1;&submin;&sub4;-Alkyl, C&sub1;&submin;&sub4;-Monohydroxyalkyl, C&sub2;&submin;&sub4;-Polyhydroxyalkyl, C&sub1;&submin;&sub4;-Aminoalkyl, C&sub1;&submin;&sub4;-Cyanoalkyl oder C&sub1;&submin;&sub4;- Alkoxy-C&sub1;&submin;&sub4;-alkyl;Rio hydrogen, fluorine, C1-4 alkyl, C1-4 monohydroxyalkyl, C2-4 polyhydroxyalkyl, C1-4 aminoalkyl, C1-4 cyanoalkyl or C1-4 alkoxy-C1-4 alkyl;
mit der Maßgabe, daß mindestens eine der Gruppen R&sub9; oder R&sub1;&sub0; Wasserstoff bedeutet.with the proviso that at least one of the groups R�9; or R₁₀ is hydrogen.
Von den p-Aminophenolen der obengenannten Formel (III) können insbesondere genannt werden: p-Aminophenol, 4-Amino-3-methylphenol, 4- Amino-3-fluorphenol, 4-Amino-3-hydroxymethylphenol, 4-Amino-2- methylphenol, 4-Amino-2-hydroxymethylphenol, 4-Amino-2-methoxymethylphenol, 4-Amino-2-aminomethylphenol, 4-Amino-2-(β-hydroxyethylaminomethyl)-phenol und die Additionssalze dieser Verbindungen mit einer Säure.Among the p-aminophenols of the abovementioned formula (III), there may be mentioned in particular: p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(β-hydroxyethylaminomethyl)phenol and the addition salts of these compounds with an acid.
- die o-Aminophenole, die als Oxidationsbasen in den erfindungsgemäßen Farbmittelzusammensetzungen verwendet werden können, sind insbesondere ausgewählt unter: 2-Aminophenol, 2-Amino-1-hydroxy- 5-methylbenzol, 2-Amino-1-hydroxy-6-methylbenzol, 5-Acetamido-2- aminophenol und den Additionssalzen dieser Verbindungen mit einer Säure.- the o-aminophenols which can be used as oxidation bases in the colorant compositions according to the invention are chosen in particular from: 2-aminophenol, 2-amino-1-hydroxy-5-methylbenzene, 2-amino-1-hydroxy-6-methylbenzene, 5-acetamido-2-aminophenol and the addition salts of these compounds with an acid.
- die heterocyclischen Basen, die als Oxidationsbasen im Rahmen der Erfindung verwendet werden können, sind insbesondere unter den Pyridinderivaten, Pyrimidinderivaten, Pyralzolderivaten und den Additionssalzen dieser Verbindungen mit einer Säure ausgewählt.- the heterocyclic bases which can be used as oxidation bases in the context of the invention are chosen in particular from pyridine derivatives, pyrimidine derivatives, pyralzole derivatives and the addition salts of these compounds with an acid.
Von den Pyridinderivaten können insbesondere die Verbindungen, die beispielsweise in den Patenten GB 1 026 978 und GB 1 153 196 beschrieben sind, wie 2,5-Diaminopyridin, und die Additionssalze dieser Verbindungen mit einer Säure genannt werden.Among the pyridine derivatives, mention may be made in particular of the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, such as 2,5-diaminopyridine, and the addition salts of these compounds with an acid.
Von den Pyrimidinderivaten können insbesondere die Verbindungen, die beispielsweise in den Patenten DE 23 59 399, JP 88-169 571 und JP 91-333 495 beschrieben sind, wie 2,4,5,6-Tetraaminopyrimidin und 4-Hydroxy-2,5,6-Triaminopyrimidin, und die Additionssalze dieser Verbindungen mit einer Säure genannt werden.Among the pyrimidine derivatives, mention may be made in particular of the compounds described, for example, in patents DE 23 59 399, JP 88-169 571 and JP 91-333 495, such as 2,4,5,6-tetraaminopyrimidine and 4-hydroxy-2,5,6-triaminopyrimidine, and the addition salts of these compounds with an acid.
Von den Pyrazolderivaten können insbesondere die Verbindungen, die in den Patenten DE 38 43 892 und DE 41 33 957 und den Patentanmeldungen WO94/08969 und WO94/08970 beschrieben sind, wie 4,5- Diamino-1-methylpyrazol, 3,4-Diamino-pyrazol und 4,5-Diamino-1-(4'- chlorbenzyl)-pyrazol, und die Additionssalze dieser Verbindungen mit einer Säure genannt werden.Among the pyrazole derivatives, mention may be made in particular of the compounds described in patents DE 38 43 892 and DE 41 33 957 and patent applications WO94/08969 and WO94/08970, such as 4,5-diamino-1-methylpyrazole, 3,4-diaminopyrazole and 4,5-diamino-1-(4'-chlorobenzyl)pyrazole, and the addition salts of these compounds with an acid.
Das Farbstoffvorprodukt eines Oxidationsfarbstoffes oder die Farbstoffvorprodukte von Oxidationsfarbstoffen machen erfindungsgemäß vorzugsweise etwa 0,0005 bis 12 Gew.-% des Gesamtgewichts der Zusammensetzung (A) und noch bevorzugter etwa 0,005 bis 6 Gew.-% aus.According to the invention, the dye precursor of an oxidation dye or the dye precursors of oxidation dyes preferably make up about 0.0005 to 12% by weight of the total weight of the composition (A) and more preferably about 0.005 to 6% by weight.
Bei den Kupplern, die in dem erfindungsgemäßen Verfahren zum Färben verwendbar sind, handelt es sich um herkömmlich in Zusammensetzungen zum oxidativen Färben verwendet Kuppler, d. h. m-Phenylendiamine, m-Aminophenole, m-Dihydroxybenzole (Resorcinole), mono- und polyhydroxylierte Naphthalinderivate, Sesamol und seine Derivate und heterocyclische Verbindungen, beispielsweise Indolkuppler, Indolinkuppler und Pyridinkuppler, und deren Additionssalze mit einer Säure.The couplers usable in the dyeing process according to the invention are couplers conventionally used in oxidative dyeing compositions, i.e. m-phenylenediamines, m-aminophenols, m-dihydroxybenzenes (resorcinols), mono- and polyhydroxylated naphthalene derivatives, sesamol and its derivatives and heterocyclic compounds, for example indole couplers, indoline couplers and pyridine couplers, and their addition salts with an acid.
Die Kuppler können insbesondere unter 2-Methyl-5-amino-phenol, 5-N- β-Hydroxyethyl)-amino-2-methylphenol, 3-Aminophenol, 1,3- Dihydroxybenzol, 1,3-Dihydroxy-2-methylbenzol, 4-Chlor-1,3- dihydroxy-benzol, 1-(β-Hydroxyethoxy)-2,4-diaminobenzol, 2-Amino-4- (β-hydroxyethylamino)-1-methoxy- benzol, 1,3-Diamino-benzol, 1,3- Bis(2,4-diaminophenoxy)-propan, Sesamol, α-Naphthol, 6-Hydroxyindol, 4-Hydroxyindol, 4-Hydroxy-N-methylindol, 6-Hydroxyindolin, 2,6- Dihydroxy-4-methylpyridin, 1-H-3-Methyl-pyrazol-5-on, 1-Phenyl-3- methylpyrazol-5-on und den Additionssalzen dieser Verbindungen mit einer Säure ausgewählt werden.The couplers can in particular be 2-methyl-5-amino-phenol, 5-N-β-hydroxyethyl)-amino-2-methylphenol, 3-aminophenol, 1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene , 4-chloro-1,3-dihydroxy-benzene, 1-(β-hydroxyethoxy)-2,4-diaminobenzene, 2-amino-4-(β-hydroxyethylamino)-1-methoxy-benzene, 1,3 -Diamino-benzene, 1,3-bis(2,4-diaminophenoxy)-propane, sesamol, α-naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 6-hydroxyindoline, 2,6 - Dihydroxy-4-methylpyridine, 1-H-3-methyl-pyrazol-5-one, 1-phenyl-3- methylpyrazol-5-one and the addition salts of these compounds with an acid.
Wenn Kuppler vorliegen, machen sie vorzugsweise etwa 0,0001 bis 10 Gew.-% des Gesamtgewichts der Zusammensetzung (A) und noch bevorzugter etwa 0,005 bis 5 Gew.-% dieses Gewichts aus.When couplers are present, they preferably represent from about 0.0001 to 10% by weight of the total weight of composition (A), and more preferably from about 0.005 to 5% by weight of that weight.
Die Additionssalze der auxochromen Verbindungen, d. h. der Oxidationsbasen und der Kuppler, mit einer Säure sind insbesondere unter den Hydrochloriden, Hydrobromiden, Sulfaten, Tartraten, Lactaten und Acetaten ausgewählt.The addition salts of the auxochromic compounds, i.e. the oxidation bases and the couplers, with an acid are chosen in particular from the hydrochlorides, hydrobromides, sulfates, tartrates, lactates and acetates.
Die Zusammensetzung (A) kann neben den oben definierten Farbstoffvorprodukten von Oxidationsfarbstoffen und gegebenenfalls vorliegenden Kupplern Direktfarbstoffe enthalten, um die Farbnuancen mit Glanz anzureichern. Die Direktfarbstoffe können insbesondere unter den nitrierten Farbstoffen, den Azofarbstoffen und den Anthrachinonfarbstoffen ausgewählt werden.Composition (A) may contain, in addition to the dye precursors of oxidation dyes defined above and optionally present couplers, direct dyes in order to enrich the colour shades with brilliance. The direct dyes may be chosen in particular from nitrated dyes, azo dyes and anthraquinone dyes.
Die Zusammensetzung (A) und/ oder die Zusammensetzung (B) können ferner mindestens ein substantives kationisches oder amphoteres Polymer enthalten, beispielsweise ein in der Patentanmeldung EP-0 673 641 definiertes Polymer, wobei vorteilhaft bevorzugt die folgenden Polymere verwendet werden:The composition (A) and/or the composition (B) may further contain at least one substantive cationic or amphoteric polymer, for example a polymer defined in patent application EP-0 673 641, the following polymers being advantageously preferably used:
- die quartären Polyammoniumpolymere, die zusammen mit ihrem Herstellungsverfahren in dem französischen Patent 2 270 846 beschrieben sind und die aus wiederkehrenden Einheiten der folgenden Formel (IV) bestehen: - the quaternary polyammonium polymers described together with their preparation process in French Patent 2 270 846 and consisting of repeating units of the following formula (IV):
insbesondere Polymere, deren mit Gel-Permeations-Chromatographie bestimmtes Gewichtsmittel des Molekulargewichts im Bereich von 9500 bis 9900 liegt;in particular polymers whose weight average molecular weight, determined by gel permeation chromatography, is in the range from 9500 to 9900;
- die quartären Polyammoniumpolymere, die zusammen mit ihrem Herstellungsverfahrens in dem französischen Patent 2 270 846 beschrieben sind und die aus wiederkehrenden Einheiten der folgenden Formel (V) bestehen: - the quaternary polyammonium polymers described together with their preparation process in French Patent 2 270 846 and consisting of repeating units of the following formula (V):
insbesondere Polymere, deren mit Gel-Permeations-Chromatographie bestimmtes Gewichtsmittel des Molekulargewichts etwa 1200 beträgt;in particular polymers whose weight average molecular weight, determined by gel permeation chromatography, is about 1200;
Das zum Färben geeignete Medium der Zusammensetzung (A) ist vorzugsweise ein wäßriges Medium, das hauptsächlich aus Wasser besteht und gegebenenfalls kosmetisch akzeptable organische Lösungsmittel enthält; von diesen können beispielsweise Alkohole, wie Ethanol, Isopropanol, Benzylalkohol und Phenylethylalkohol, Glykole oder Glykolether, wie Ethylenglykolmonomethylether, Ethylenglykolmonoethylether und Ethylenglykolmonobutylether, Propylenglykol oder seine Ether, wie Propylenglykolmonomethylether, Butylenglykol, Dipropylenglykol sowie die Diethylenglykolalkylether, beispielsweise Diethylenglykolrnonomethylether und Diethylenglykolmonobutylether, in Konzentrationen im Bereich von etwa 0,5 bis 20 Gew.-%, bezogen auf das Gesamtgewicht der Zusammensetzung, und vorzugsweise im Bereich von etwa 2 bis 10 Gew.-% verwendet werden.The medium suitable for coloring of composition (A) is preferably an aqueous medium consisting mainly of water and optionally containing cosmetically acceptable organic solvents; among these, for example, alcohols such as ethanol, isopropanol, benzyl alcohol and phenylethyl alcohol, glycols or glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether and ethylene glycol monobutyl ether, propylene glycol or its ethers such as propylene glycol monomethyl ether, butylene glycol, dipropylene glycol and the diethylene glycol alkyl ethers such as diethylene glycol monomethyl ether and diethylene glycol monobutyl ether, in concentrations ranging from about 0.5 to 20% by weight relative to the total weight of the composition, and preferably from about 2 to 10% by weight.
Die Zusammensetzung (A) und/oder die Zusammensetzung (B) können auch weitere, häufig in der Kosmetik verwendete Mittel in wirksamen Mengen enthalten. Bei diesen Zusatzstoffen handelt es sich beispielsweise um Maskierungsmittel, Konditioniermittel für das Haar und insbesondere Silicone, Konservierungsmittel, Trübungsmittel und dergleichen und gegebenenfalls anionische, nichtionische oder amphotere grenzflächenaktive Stoffe oder deren Gemische.Composition (A) and/or composition (B) may also contain other agents frequently used in cosmetics in effective amounts. These additives include, for example, masking agents, hair conditioners and, in particular, silicones, preservatives, opacifiers and the like, and optionally anionic, non-ionic or amphoteric surfactants or mixtures thereof.
Die Farbmittelzusammensetzung kann auch Antioxidantien enthalten. Diese können insbesondere unter Natriumsulfit, Thioglykolsäure, Thiomilchsäure, Natriumbisulfit, Dehydroascorbinsäure, Hydrochinon, 2- Methyi-hydrochinon, tert.-Butyl-hydrochinon und Homogentisinsäure ausgewählt werden; sie liegen gegebenenfalls in Mengenanteilen im Bereich von etwa 0,05 bis 3,0 Gew.-%, bezogen auf das Gesamtgewicht der Zusammensetzung, vor.The colorant composition may also contain antioxidants. These may be selected in particular from sodium sulfite, thioglycolic acid, thiolactic acid, sodium bisulfite, dehydroascorbic acid, hydroquinone, 2- methylhydroquinone, tert-butylhydroquinone and homogentisic acid; they are optionally present in proportions in the range of about 0.05 to 3.0% by weight, based on the total weight of the composition.
Der Fachmann wird selbstverständlich die oben genannte(n), gegebenenfalls vorliegende(n) zusätzliche(n) Verbindung(en) so auswählen, daß die mit der erfindungsgemäßen Farbmittelzusammensetzung verbundenen vorteilhaften Eigenschaften durch den beabsichtigten Zusatz oder die Zusätze nicht oder im wesentlichen nicht verändert werden.The person skilled in the art will of course select the above-mentioned, optionally present additional compound(s) in such a way that the advantageous properties associated with the colorant composition according to the invention are not or substantially not changed by the intended additive or additives.
Das Oxidationsmittel in der Zusammensetzung (B) ist vorzugsweise unter Wasserstoffperoxid, Harnstoffperoxid, Bromaten oder Ferricyaniden von Alkalimetallen und Salzen von Persäuren, wie Perboraten, Percarbonaten und Persulfaten ausgewählt. Wasserstoffperoxid wird besonders bevorzugt.The oxidizing agent in composition (B) is preferably selected from hydrogen peroxide, urea peroxide, bromates or ferricyanides of alkali metals and salts of peracids such as perborates, percarbonates and persulfates. Hydrogen peroxide is particularly preferred.
Die Zusammensetzung (B) besteht vorteilhaft aus einer Wasserstoffperoxidlösung, deren Titer vorzugsweise im Bereich von etwa 2,5 bis 40 Volumina und insbesondere 5 bis 20 Volumina liegt.The composition (B) advantageously consists of a hydrogen peroxide solution whose titre is preferably in the range of about 2.5 to 40 volumes and in particular 5 to 20 volumes.
Der pH-Wert der gebrauchsfertigen Zusammensetzung nach dem Mischen der Farbmittelzusammensetzung (A) und der oxidierenden Zusammensetzung (B) liegt im allgemeinen im Bereich von 4 bis 11 und vorzugsweise 6 bis 10,5. Er kann mit üblicherweise beim Färben von Keratinfasern verwendeten Mitteln zum Ansäuern oder Alkalischmachen auf den gewünschten Wert eingestellt werden.The pH of the ready-to-use composition after mixing the dye composition (A) and the oxidizing composition (B) is generally in the range from 4 to 11 and preferably from 6 to 10.5. It can be adjusted to the desired value using acidifying or alkalizing agents commonly used in dyeing keratin fibers.
Von den Mitteln zum Alkalischmachen können beispielsweise Ammoniak, Alkalicarbonate, Alkanolamine, wie Mono-, Di- und Triethanolamin, sowie deren Derivate, Natriumhydroxid oder Kaliumhydroxid und Verbindungen der folgenden Formel (VI) genannt werden: Examples of alkalinizing agents include ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamine, and their derivatives, sodium hydroxide or potassium hydroxide and compounds of the following formula (VI):
worin bedeuten:where:
R eine gegebenenfalls mit einer Hydroxygruppe oder einer C&sub1;&submin;&sub4;-Alkylgruppe substituierte Propylengruppe und R&sub1;&sub1;, R&sub1;&sub2;, R&sub1;&sub3; und R&sub1;&sub4;, die identisch oder voneinander verschieden sind, ein Wasserstoffatom, eine C&sub1;&submin;&sub4;- Alkylgruppe oder eine C&sub1;&submin;&sub4;-Hydroxyalkylgruppe.R represents a propylene group optionally substituted by a hydroxy group or a C₁₋₄-alkyl group, and R₁₁, R₁₂, R₁₃ and R₁₄, which are identical or different from each other, represent a hydrogen atom, a C₁₋₄-alkyl group or a C₁₋₄-hydroxyalkyl group.
Die Ansäuerungsmittel sind herkömmlich beispielsweise anorganische oder organische Säuren, wie Salzsäure, Orthophosphorsäure, Carbonsäuren, wie Weinsäure, Citronensäure und Milchsäure, und Sulfonsäuren.The acidifying agents are conventionally, for example, inorganic or organic acids, such as hydrochloric acid, orthophosphoric acid, carboxylic acids, such as tartaric acid, citric acid and lactic acid, and sulfonic acids.
Das erfindungsgemäße Verfahren zum Färben besteht vorzugsweise darin, ein Gemisch, das kurz vor der Anwendung aus den oben beschriebenen Zusammensetzungen (A) und (B) hergestellt wird, auf die trockenen oder feuchten Keratinfasern aufzutragen und während einer Zeitspanne von vorzugsweise etwa 1 bis 60 min und noch bevorzugter etwa 10 bis 45 min einwirken zu lassen, dann die Fasern zu spülen, gegebenenfalls mit Haarwaschmittel zu waschen, von neuem zu spülen und die Fasern zu trocknen.The dyeing process according to the invention preferably consists in preparing a mixture which, shortly before use, consists of the above described compositions (A) and (B) to the dry or wet keratin fibres and leave to act for a period of time of preferably about 1 to 60 minutes and more preferably about 10 to 45 minutes, then rinse the fibres, wash them with shampoo if necessary, rinse them again and dry the fibres.
Die vorstehende Beschreibung dient natürlich nur zur Erläuterung und ist nicht einschränkend zu verstehen; Variationen und Modifikationen können im Rahmen der Erfindung natürlich durchgeführt werden.The foregoing description is of course only illustrative and is not to be understood as limiting; variations and modifications can of course be made within the scope of the invention.
Die folgenden Beispiele erläutern die Erfindung, ohne sie einzuschränken.The following examples illustrate the invention without limiting it.
Es wird die folgende Farbmittelzusammensetzung hergestellt:The following colorant composition is produced:
- ethoxylierter (3) Decylalkohol 9%- ethoxylated (3) decyl alcohol 9%
- Oleylalkohol 6%- Oleyl alcohol 6%
- Ölsäure 3%- Oleic acid 3%
- Alkylpolyglycosid (1.4) 6,9%- Alkyl polyglycoside (1.4) 6.9%
- Ethanol 6,5%- Ethanol 6.5%
- Ethylenglykolmonobutylether 10%- Ethylene glycol monobutyl ether 10%
- quaternisierte Laurylhydroxyethylcellulose (unter der Bezeichnung Quatrisoft LM 200 vöm Amerchol erhältlich) 0,2%- quaternized lauryl hydroxyethyl cellulose (available under the name Quatrisoft LM 200 from Amerchol) 0.2%
- Maskierungsmittel qs- Masking agent qs
- Reduktionsmittel qs- Reducing agent qs
- Parfum qs- Perfume qs
- Antioxidationsmittel qs- Antioxidant qs
- Ammoniak von 20% 10%- Ammonia from 20% 10%
- 1,3-Dihydroxybenzol 0,4%- 1,3-dihydroxybenzene 0.4%
- 3-Aminophenol 0,074%- 3-Aminophenol 0.074%
- 1-(β-Hydroxyethoxy)-2,4-diaminobenzol-Hydrochlorid 0,0094%- 1-(β-Hydroxyethoxy)-2,4-diaminobenzene hydrochloride 0.0094%
- 1,3-Dihydroxy-2-methylbenzol 0,15%- 1,3-Dihydroxy-2-methylbenzene 0.15%
- N,N'-Bis(β-hydroxyethyl)-N,N'-bis(4-aminophenyl)-1,3-di- 0,1% amino-2-propanol-Tetrahydrochlorid- N,N'-Bis(β-hydroxyethyl)-N,N'-bis(4-aminophenyl)-1,3-di-0.1% amino-2-propanol tetrahydrochloride
- p-Phenylendiamin 0,63- p-Phenylenediamine 0.63
- entmineralisiertes Wasser ad 100%- demineralized water ad 100%
Bei der Anwendung wird die Farbmittelzusammensetzung mit der gleichen Gewichtsmenge einer Wasserstoffperoxidlösung (20 Volumina, 6 Gew.-%) vermischt.During application, the colorant composition is mixed with an equal amount by weight of a hydrogen peroxide solution (20 volumes, 6% by weight).
Das erhaltene Gemisch wird 30 min auf Strähnen von natürlichem grauen Haar mit 90% weißen Haaren aufgebracht. Dann werden die Strähnen gespült, mit Standardhaarwaschmittel gewaschen, nochmals gespült und getrocknet.The resulting mixture is applied to strands of natural gray hair with 90% white hair for 30 minutes. Then the strands are rinsed, washed with standard shampoo, rinsed again and dried.
Man erhält eine hellbraune Farbnuance.You get a light brown color nuance.
Claims (22)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| FR9802775 | 1998-03-06 |
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| DE69900441T2 true DE69900441T2 (en) | 2002-07-18 |
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| DE69900441T Expired - Lifetime DE69900441T2 (en) | 1998-03-06 | 1999-03-02 | Oxidative dyeing process and composition for oxidative dyeing of keratin fibers containing a cationic amphiphilic polymer |
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| EP (1) | EP0943320B1 (en) |
| JP (1) | JPH11292745A (en) |
| KR (1) | KR100335259B1 (en) |
| CN (2) | CN1255092C (en) |
| AR (1) | AR017725A1 (en) |
| AT (1) | ATE208605T1 (en) |
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| BR (1) | BR9900667B1 (en) |
| CA (1) | CA2263037C (en) |
| DE (1) | DE69900441T2 (en) |
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| ES (1) | ES2163320T3 (en) |
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| PL (1) | PL195678B1 (en) |
| PT (1) | PT943320E (en) |
| RU (1) | RU2167645C2 (en) |
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| JP3294767B2 (en) | 1996-07-25 | 2002-06-24 | ホーユー株式会社 | Hair dye composition |
| FR2753093B1 (en) * | 1996-09-06 | 1998-10-16 | Oreal | COMPOSITION OF OXIDIZING DYE FOR KERATINIC FIBERS CONTAINING AN ANIONIC AMPHIPHILIC POLYMER |
| FR2753094B1 (en) * | 1996-09-06 | 1998-10-16 | Oreal | COMPOSITION OF OXIDIZING DYE FOR KERATINIC FIBERS CONTAINING AN ANIONIC AMPHIPHILIC POLYMER |
| US5961990A (en) * | 1997-05-02 | 1999-10-05 | Kobo Products S.A.R.L. | Cosmetic particulate gel delivery system and method of preparing complex gel particles |
| FR2773477B1 (en) * | 1998-01-13 | 2001-02-23 | Oreal | TINCTORIAL COMPOSITION AND METHODS FOR DYEING KERATINIC FIBERS USING THE SAME |
| FR2803197B1 (en) * | 1999-12-30 | 2002-03-15 | Oreal | COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING A THICKENING POLYMER COMPRISING AT LEAST ONE FATTY CHAIN AND A FATTY ALCOHOL HAVING MORE THAN TWENTY CARBON ATOMS |
-
1999
- 1999-02-22 PL PL331578A patent/PL195678B1/en unknown
- 1999-02-23 AU AU18353/99A patent/AU707586B1/en not_active Ceased
- 1999-02-25 CA CA002263037A patent/CA2263037C/en not_active Expired - Fee Related
- 1999-03-02 DK DK99400505T patent/DK0943320T3/en active
- 1999-03-02 ES ES99400505T patent/ES2163320T3/en not_active Expired - Lifetime
- 1999-03-02 AT AT99400505T patent/ATE208605T1/en active
- 1999-03-02 PT PT99400505T patent/PT943320E/en unknown
- 1999-03-02 DE DE69900441T patent/DE69900441T2/en not_active Expired - Lifetime
- 1999-03-02 EP EP99400505A patent/EP0943320B1/en not_active Expired - Lifetime
- 1999-03-03 AR ARP990100891A patent/AR017725A1/en active IP Right Grant
- 1999-03-04 BR BRPI9900667-7A patent/BR9900667B1/en not_active IP Right Cessation
- 1999-03-05 HU HU9900547A patent/HU223406B1/en not_active IP Right Cessation
- 1999-03-05 RU RU99104501/14A patent/RU2167645C2/en not_active IP Right Cessation
- 1999-03-05 KR KR1019990007222A patent/KR100335259B1/en not_active IP Right Cessation
- 1999-03-06 CN CNB2004100351803A patent/CN1255092C/en not_active Expired - Lifetime
- 1999-03-06 CN CNB991034368A patent/CN1204869C/en not_active Expired - Lifetime
- 1999-03-08 JP JP11059945A patent/JPH11292745A/en active Pending
- 1999-03-08 US US09/263,954 patent/US6673124B2/en not_active Expired - Lifetime
-
2004
- 2004-01-05 US US10/750,987 patent/US20040187230A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ATE208605T1 (en) | 2001-11-15 |
| AU707586B1 (en) | 1999-07-15 |
| EP0943320B1 (en) | 2001-11-14 |
| US20030188392A1 (en) | 2003-10-09 |
| CA2263037C (en) | 2005-07-12 |
| KR19990077608A (en) | 1999-10-25 |
| CA2263037A1 (en) | 1999-09-06 |
| KR100335259B1 (en) | 2002-05-02 |
| HU9900547D0 (en) | 1999-05-28 |
| US20040187230A1 (en) | 2004-09-30 |
| HUP9900547A3 (en) | 2000-12-28 |
| EP0943320A1 (en) | 1999-09-22 |
| HUP9900547A2 (en) | 2000-01-28 |
| PL195678B1 (en) | 2007-10-31 |
| DE69900441D1 (en) | 2001-12-20 |
| CN1552302A (en) | 2004-12-08 |
| CN1255092C (en) | 2006-05-10 |
| CN1229640A (en) | 1999-09-29 |
| PL331578A1 (en) | 1999-09-13 |
| ES2163320T3 (en) | 2002-01-16 |
| BR9900667A (en) | 2000-05-02 |
| HU223406B1 (en) | 2004-06-28 |
| PT943320E (en) | 2002-04-29 |
| RU2167645C2 (en) | 2001-05-27 |
| AR017725A1 (en) | 2001-09-12 |
| BR9900667B1 (en) | 2010-02-23 |
| CN1204869C (en) | 2005-06-08 |
| US6673124B2 (en) | 2004-01-06 |
| DK0943320T3 (en) | 2002-02-25 |
| JPH11292745A (en) | 1999-10-26 |
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